#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/28/7152802.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7152802
loop_
_publ_author_name
'Sartori, Glaubia'
'Neto, José S S'
'Pesarico, Ana Paula'
'Back, Davi F.'
'Nogueira, Cristina W.'
'Zeni, Gilson'
_publ_section_title
;
 Bis-vinyl selenides obtained via iron(iii) catalyzed addition of PhSeSePh
 to alkynes: synthesis and antinociceptive activity.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1199
_journal_page_last               1208
_journal_paper_doi               10.1039/c2ob27064a
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C28 H18 F6 Se2'
_chemical_formula_sum            'C28 H18 F6 Se2'
_chemical_formula_weight         626.34
_chemical_melting_point          ?
_chemical_name_common            (E)-1,2-diphenyl-1,2-bis(3-(trifluoromethyl)p
_chemical_name_systematic
;
(E)-1,2-diphenyl-1,2-bis(3-(trifluoromethyl)phenylselanyl)ethene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2012-04-17T17:19:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 117.181(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.4735(9)
_cell_length_b                   5.6000(3)
_cell_length_c                   16.5182(10)
_cell_measurement_reflns_used    2767
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.0275
_cell_measurement_theta_min      2.475
_cell_volume                     1273.26(13)
_computing_cell_refinement       'BRUKER SANT'
_computing_data_collection       'BRUKER APEX-II'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18356
_diffrn_reflns_theta_full        27.29
_diffrn_reflns_theta_max         27.29
_diffrn_reflns_theta_min         1.48
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    2.963
_exptl_absorpt_correction_T_max  0.8423
_exptl_absorpt_correction_T_min  0.5246
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.106
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[σ²(Fo²)+(0.0346P)²+1.6978P] where
P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                1531
_reflns_number_total             2747
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2ob27064a.txt
_cod_data_source_block           p21c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'none' was changed to '?' - the value
is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7152802
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Se Se 0.96558(3) 0.26214(9) 0.87922(3) 0.0646(2) Uani 1 1 d .
F1 F 0.5771(3) 0.3162(11) 0.7061(3) 0.192(3) Uani 1 1 d .
F2 F 0.5249(3) 0.0071(11) 0.6395(5) 0.213(3) Uani 1 1 d .
F3 F 0.5519(3) 0.2784(11) 0.5749(3) 0.183(2) Uani 1 1 d .
C8 C 0.9603(3) 0.0479(8) 0.9697(3) 0.0541(11) Uani 1 1 d .
C9 C 0.8611(3) 0.0203(7) 0.9638(3) 0.0483(10) Uani 1 1 d .
C14 C 0.8048(3) -0.1755(8) 0.9213(3) 0.0593(12) Uani 1 1 d .
H14 H 0.8307 -0.3 0.902 0.071 Uiso 1 1 calc R
C13 C 0.7095(3) -0.1871(9) 0.9073(3) 0.0680(13) Uani 1 1 d .
H13 H 0.6714 -0.3188 0.8781 0.082 Uiso 1 1 calc R
C12 C 0.6718(3) -0.0062(10) 0.9361(4) 0.0750(15) Uani 1 1 d .
H12 H 0.6074 -0.0131 0.9256 0.09 Uiso 1 1 calc R
C11 C 0.7281(4) 0.1858(9) 0.9804(4) 0.0734(14) Uani 1 1 d .
H11 H 0.7026 0.3072 1.0015 0.088 Uiso 1 1 calc R
C10 C 0.8226(3) 0.1996(8) 0.9938(3) 0.0633(12) Uani 1 1 d .
H10 H 0.8605 0.3314 1.0233 0.076 Uiso 1 1 calc R
C1 C 0.8577(3) 0.1158(8) 0.7776(3) 0.0572(11) Uani 1 1 d .
C6 C 0.8733(4) -0.0790(9) 0.7357(3) 0.0723(14) Uani 1 1 d .
H6 H 0.9363 -0.1327 0.7537 0.087 Uiso 1 1 calc R
C5 C 0.7962(5) -0.1957(10) 0.6672(4) 0.0856(17) Uani 1 1 d .
H5 H 0.8073 -0.3277 0.6391 0.103 Uiso 1 1 calc R
C4 C 0.7028(4) -0.1168(11) 0.6405(3) 0.0823(15) Uani 1 1 d .
H4 H 0.6505 -0.196 0.5947 0.099 Uiso 1 1 calc R
C3 C 0.6873(3) 0.0804(9) 0.6822(3) 0.0660(13) Uani 1 1 d .
C7 C 0.5880(4) 0.1715(14) 0.6528(4) 0.097(2) Uani 1 1 d .
C2 C 0.7645(3) 0.1987(8) 0.7496(3) 0.0576(12) Uani 1 1 d .
H2 H 0.7538 0.3345 0.7762 0.069 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se 0.0428(3) 0.0784(4) 0.0677(3) 0.0198(3) 0.0210(2) -0.0072(2)
F1 0.068(3) 0.317(7) 0.149(4) -0.089(4) 0.014(2) 0.067(3)
F2 0.072(3) 0.200(6) 0.354(9) -0.003(6) 0.088(4) -0.025(3)
F3 0.092(3) 0.307(7) 0.133(4) 0.077(4) 0.036(3) 0.089(4)
C8 0.046(3) 0.055(3) 0.060(3) -0.009(2) 0.023(2) -0.006(2)
C9 0.032(2) 0.055(3) 0.054(3) 0.000(2) 0.018(2) -0.0019(19)
C14 0.049(3) 0.054(3) 0.073(3) -0.007(2) 0.025(2) -0.006(2)
C13 0.046(3) 0.070(4) 0.080(3) 0.002(3) 0.021(3) -0.015(2)
C12 0.040(3) 0.086(4) 0.100(4) 0.019(3) 0.033(3) 0.000(3)
C11 0.069(4) 0.067(4) 0.105(4) 0.007(3) 0.057(3) 0.009(3)
C10 0.061(3) 0.055(3) 0.085(3) -0.011(2) 0.043(3) -0.013(2)
C1 0.053(3) 0.064(3) 0.059(3) 0.011(2) 0.030(2) 0.005(2)
C6 0.075(4) 0.081(4) 0.072(3) 0.012(3) 0.043(3) 0.024(3)
C5 0.106(5) 0.071(4) 0.083(4) -0.012(3) 0.045(4) 0.014(3)
C4 0.078(4) 0.093(4) 0.065(3) -0.011(3) 0.024(3) -0.011(3)
C3 0.050(3) 0.085(4) 0.056(3) 0.004(3) 0.018(2) 0.005(3)
C7 0.048(4) 0.152(6) 0.074(4) -0.006(4) 0.012(3) 0.007(4)
C2 0.047(3) 0.064(3) 0.060(3) 0.004(2) 0.023(2) 0.009(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C1 Se C8 94.78(18) .
C8 C8 C9 126.1(5) 3_757
C8 C8 Se 119.4(4) 3_757
C9 C8 Se 114.4(3) .
C10 C9 C14 119.3(4) .
C10 C9 C8 120.1(4) .
C14 C9 C8 120.3(4) .
C9 C14 C13 120.0(4) .
C9 C14 H14 120 .
C13 C14 H14 120 .
C12 C13 C14 120.1(4) .
C12 C13 H13 119.9 .
C14 C13 H13 119.9 .
C13 C12 C11 120.2(4) .
C13 C12 H12 119.9 .
C11 C12 H12 119.9 .
C12 C11 C10 120.0(5) .
C12 C11 H11 120 .
C10 C11 H11 120 .
C9 C10 C11 120.4(4) .
C9 C10 H10 119.8 .
C11 C10 H10 119.8 .
C6 C1 C2 119.8(5) .
C6 C1 Se 119.8(4) .
C2 C1 Se 120.4(4) .
C1 C6 C5 120.5(5) .
C1 C6 H6 119.8 .
C5 C6 H6 119.8 .
C6 C5 C4 119.9(5) .
C6 C5 H5 120 .
C4 C5 H5 120 .
C5 C4 C3 119.6(5) .
C5 C4 H4 120.2 .
C3 C4 H4 120.2 .
C2 C3 C4 120.3(5) .
C2 C3 C7 119.3(5) .
C4 C3 C7 120.4(5) .
F1 C7 F2 104.2(6) .
F1 C7 F3 105.3(7) .
F2 C7 F3 102.3(6) .
F1 C7 C3 116.3(5) .
F2 C7 C3 113.8(6) .
F3 C7 C3 113.5(6) .
C3 C2 C1 119.9(4) .
C3 C2 H2 120 .
C1 C2 H2 120 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se C1 1.927(5) .
Se C8 1.947(4) .
F1 C7 1.263(7) .
F2 C7 1.286(8) .
F3 C7 1.293(7) .
C8 C8 1.294(8) 3_757
C8 C9 1.501(5) .
C9 C10 1.370(6) .
C9 C14 1.377(5) .
C14 C13 1.385(6) .
C14 H14 0.93 .
C13 C12 1.360(7) .
C13 H13 0.93 .
C12 C11 1.367(7) .
C12 H12 0.93 .
C11 C10 1.378(6) .
C11 H11 0.93 .
C10 H10 0.93 .
C1 C6 1.370(6) .
C1 C2 1.379(6) .
C6 C5 1.377(7) .
C6 H6 0.93 .
C5 C4 1.377(7) .
C5 H5 0.93 .
C4 C3 1.379(7) .
C4 H4 0.93 .
C3 C2 1.375(6) .
C3 C7 1.475(7) .
C2 H2 0.93 .
